NPASS Compound

Structure

NPC114806 OpenBabel07101719142D 60 61 0 0 1 0 0 0 0 0999 V2000 -2.9625 1.8079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8197 5.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5517 5.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2426 5.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0350 -1.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4454 2.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2838 2.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 1.1721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8818 3.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8818 4.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0158 2.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0307 1.3117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9229 0.8602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0158 4.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1498 3.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1935 0.7647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9536 4.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0876 4.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1401 5.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8569 4.3870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7601 1.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6857 4.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2838 4.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8197 4.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5517 4.6068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5859 4.8787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9250 -0.4314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1498 4.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2216 4.1068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3013 1.2163 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7642 5.5111 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2541 1.5228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4177 4.1068 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3085 3.4948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9265 -0.3763 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7339 5.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8872 -0.1593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5998 2.1707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7541 0.6568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4921 6.4733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7078 -1.3521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4895 1.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4344 2.5010 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.3818 1.0510 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6524 0.9556 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5722 3.1703 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7090 0.4105 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7581 5.6211 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4458 2.5042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2629 3.7933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1102 6.3289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3140 -1.0637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5903 2.0333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5260 0.0210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4773 6.7188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1894 7.1901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4435 -2.0294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2466 -1.6506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4177 3.1068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 24 1 0 0 0 0 6 50 1 0 0 0 0 7 60 1 0 0 0 0 8 32 2 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 21 1 0 0 0 0 14 28 2 0 0 0 0 15 28 1 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 19 20 1 0 0 0 0 19 31 1 0 0 0 0 20 34 1 0 0 0 0 21 45 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 23 28 1 0 0 0 0 25 3 1 6 0 0 0 25 33 1 0 0 0 0 26 4 1 1 0 0 0 26 29 1 0 0 0 0 26 36 1 0 0 0 0 27 5 1 1 0 0 0 27 35 1 0 0 0 0 27 37 1 0 0 0 0 29 18 1 6 0 0 0 29 46 1 0 0 0 0 30 16 1 6 0 0 0 30 38 1 0 0 0 0 30 47 1 0 0 0 0 31 40 1 6 0 0 0 31 48 1 0 0 0 0 32 39 1 0 0 0 0 32 50 1 0 0 0 0 33 23 1 6 0 0 0 33 60 1 0 0 0 0 34 50 1 0 0 0 0 34 51 2 0 0 0 0 35 41 1 6 0 0 0 35 49 1 0 0 0 0 36 48 2 3 0 0 0 36 52 1 0 0 0 0 37 47 2 3 0 0 0 37 53 1 0 0 0 0 38 46 2 3 0 0 0 38 54 1 0 0 0 0 39 49 2 3 0 0 0 39 55 1 0 0 0 0 40 56 2 0 0 0 0 40 57 1 0 0 0 0 41 58 2 0 0 0 0 41 59 1 0 0 0 0 42 43 2 0 0 0 0 42 44 1 0 0 0 0 42 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	838.46
Volume:	856.841
LogP:	0.384
LogD:	0.261
LogS:	-3.107
# Rotatable Bonds:	15
TPSA:	282.44
# H-Bond Aceptor:	18
# H-Bond Donor:	10
# Rings:	2
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.042
Synthetic Accessibility Score:	5.959
Fsp3:	0.524
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.473
MDCK Permeability:	4.721426194009837e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.968
20% Bioavailability (F20%):	0.337
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	50.31466293334961%
Volume Distribution (VD):	0.303
Pgp-substrate:	45.06136703491211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.159
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	2.13
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.402
Drug-inuced Liver Injury (DILI):	0.144
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.368
Maximum Recommended Daily Dose:	0.223
Skin Sensitization:	0.131
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.168

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC114806

Natural Product ID:	NPC114806
*Common Name:**	Nodularin-Har
IUPAC Name:	(2Z,5R,6S,9S,12S,13S,16R)-9-[4-(diaminomethylideneamino)butyl]-2-ethylidene-12-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentazacyclononadecane-5,16-dicarboxylic acid
Synonyms:	Nodularin-Har
Standard InCHIKey:	YCFHEUGHSRSOFR-LTNJPURBSA-N
Standard InCHI:	InChI=1S/C42H62N8O10/c1-8-32-39(55)49-35(41(58)59)27(5)37(53)47-30(16-12-13-21-45-42(43)44)38(54)46-29(26(4)36(52)48-31(40(56)57)19-20-34(51)50(32)6)18-17-24(2)22-25(3)33(60-7)23-28-14-10-9-11-15-28/h8-11,14-15,17-18,22,25-27,29-31,33,35H,12-13,16,19-21,23H2,1-7H3,(H,46,54)(H,47,53)(H,48,52)(H,49,55)(H,56,57)(H,58,59)(H4,43,44,45)/b18-17+,24-22+,32-8-/t25-,26-,27-,29-,30-,31+,33-,35+/m0/s1
SMILES:	CO[C@H]([C@H](/C=C(/C=C/[C@@H]1N=C(O)[C@H](CCCCNC(=N)N)N=C(O)[C@@H](C)[C@@H](N=C(/C(=C/C)/N(C(=O)CC[C@@H](N=C([C@H]1C)O)C(=O)O)C)O)C(=O)O)C)C)Cc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504938
PubChem CID:	10629347
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33236	0dularia	Genus	Unionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170690]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	0.07	mg.kg-1	PMID[544753]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC114806 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	889
0.2-0.3	5232
0.3-0.4	18262
0.4-0.5	14830
0.5-0.6	2541
0.6-0.7	608
0.7-0.8	160
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC24617
0.9	High Similarity	NPC300443
0.8129	Intermediate Similarity	NPC311658
0.8075	Intermediate Similarity	NPC1390
0.8075	Intermediate Similarity	NPC62104
0.7975	Intermediate Similarity	NPC475168
0.7975	Intermediate Similarity	NPC7817
0.7953	Intermediate Similarity	NPC473404
0.7879	Intermediate Similarity	NPC22883
0.7879	Intermediate Similarity	NPC5719
0.7879	Intermediate Similarity	NPC210377
0.7879	Intermediate Similarity	NPC217804
0.7841	Intermediate Similarity	NPC240130
0.7841	Intermediate Similarity	NPC61332
0.7831	Intermediate Similarity	NPC15068
0.7826	Intermediate Similarity	NPC470902
0.7784	Intermediate Similarity	NPC63040
0.7764	Intermediate Similarity	NPC473341
0.7692	Intermediate Similarity	NPC274198
0.7692	Intermediate Similarity	NPC276506
0.7692	Intermediate Similarity	NPC198254
0.7662	Intermediate Similarity	NPC314835
0.7633	Intermediate Similarity	NPC473000
0.7633	Intermediate Similarity	NPC129486
0.7586	Intermediate Similarity	NPC475564
0.7586	Intermediate Similarity	NPC475409
0.7586	Intermediate Similarity	NPC170302
0.7584	Intermediate Similarity	NPC102959
0.7576	Intermediate Similarity	NPC324850
0.7542	Intermediate Similarity	NPC60516
0.7514	Intermediate Similarity	NPC196243
0.75	Intermediate Similarity	NPC475532
0.7486	Intermediate Similarity	NPC472999
0.7485	Intermediate Similarity	NPC469901
0.7485	Intermediate Similarity	NPC46009
0.7473	Intermediate Similarity	NPC477638
0.7473	Intermediate Similarity	NPC477632
0.7471	Intermediate Similarity	NPC473546
0.7459	Intermediate Similarity	NPC477551
0.7457	Intermediate Similarity	NPC165285
0.7455	Intermediate Similarity	NPC473580
0.7452	Intermediate Similarity	NPC132636
0.7438	Intermediate Similarity	NPC316008
0.7438	Intermediate Similarity	NPC313867
0.7425	Intermediate Similarity	NPC469898
0.7418	Intermediate Similarity	NPC302715
0.7405	Intermediate Similarity	NPC163392
0.7405	Intermediate Similarity	NPC239762
0.7391	Intermediate Similarity	NPC314358
0.7386	Intermediate Similarity	NPC311753
0.7375	Intermediate Similarity	NPC315283
0.7375	Intermediate Similarity	NPC314388
0.7363	Intermediate Similarity	NPC477631
0.7362	Intermediate Similarity	NPC2501
0.7356	Intermediate Similarity	NPC477462
0.7356	Intermediate Similarity	NPC17698
0.7351	Intermediate Similarity	NPC477550
0.7351	Intermediate Similarity	NPC477552
0.7333	Intermediate Similarity	NPC94862
0.733	Intermediate Similarity	NPC194671
0.733	Intermediate Similarity	NPC269750
0.7329	Intermediate Similarity	NPC315266
0.7326	Intermediate Similarity	NPC280022
0.7314	Intermediate Similarity	NPC469900
0.731	Intermediate Similarity	NPC61004
0.7296	Intermediate Similarity	NPC48202
0.7288	Intermediate Similarity	NPC153554
0.7283	Intermediate Similarity	NPC475204
0.7283	Intermediate Similarity	NPC475123
0.7278	Intermediate Similarity	NPC471265
0.7278	Intermediate Similarity	NPC475544
0.7278	Intermediate Similarity	NPC127741
0.7278	Intermediate Similarity	NPC471264
0.7278	Intermediate Similarity	NPC469243
0.7273	Intermediate Similarity	NPC162104
0.7267	Intermediate Similarity	NPC476978
0.7262	Intermediate Similarity	NPC197743
0.7262	Intermediate Similarity	NPC297145
0.7257	Intermediate Similarity	NPC279871
0.7253	Intermediate Similarity	NPC477636
0.725	Intermediate Similarity	NPC168113
0.7229	Intermediate Similarity	NPC122590
0.7225	Intermediate Similarity	NPC66490
0.7216	Intermediate Similarity	NPC50016
0.7205	Intermediate Similarity	NPC77905
0.7205	Intermediate Similarity	NPC197682
0.7193	Intermediate Similarity	NPC471053
0.7193	Intermediate Similarity	NPC471051
0.7193	Intermediate Similarity	NPC471052
0.7184	Intermediate Similarity	NPC40234
0.7181	Intermediate Similarity	NPC469443
0.7178	Intermediate Similarity	NPC314114
0.7176	Intermediate Similarity	NPC471527
0.716	Intermediate Similarity	NPC52748
0.7159	Intermediate Similarity	NPC158277
0.7151	Intermediate Similarity	NPC477639
0.7151	Intermediate Similarity	NPC223207
0.7143	Intermediate Similarity	NPC469903
0.7143	Intermediate Similarity	NPC263493
0.7143	Intermediate Similarity	NPC269398
0.7135	Intermediate Similarity	NPC119652
0.7135	Intermediate Similarity	NPC73655
0.7135	Intermediate Similarity	NPC97526
0.7134	Intermediate Similarity	NPC246079
0.7134	Intermediate Similarity	NPC329761
0.7134	Intermediate Similarity	NPC225648
0.7117	Intermediate Similarity	NPC5620
0.711	Intermediate Similarity	NPC471771
0.711	Intermediate Similarity	NPC290755
0.711	Intermediate Similarity	NPC304074
0.7102	Intermediate Similarity	NPC306804
0.7102	Intermediate Similarity	NPC248670
0.7099	Intermediate Similarity	NPC176226
0.7099	Intermediate Similarity	NPC139326
0.7097	Intermediate Similarity	NPC319766
0.7089	Intermediate Similarity	NPC287401
0.7081	Intermediate Similarity	NPC476259
0.7076	Intermediate Similarity	NPC469902
0.7069	Intermediate Similarity	NPC107938
0.7069	Intermediate Similarity	NPC294516
0.7062	Intermediate Similarity	NPC471165
0.7052	Intermediate Similarity	NPC63931
0.7051	Intermediate Similarity	NPC469666
0.7032	Intermediate Similarity	NPC477937
0.703	Intermediate Similarity	NPC135121
0.7024	Intermediate Similarity	NPC56685
0.7019	Intermediate Similarity	NPC92784
0.7019	Intermediate Similarity	NPC476133
0.7019	Intermediate Similarity	NPC470884
0.7019	Intermediate Similarity	NPC178662
0.7019	Intermediate Similarity	NPC98424
0.7012	Intermediate Similarity	NPC209509
0.7012	Intermediate Similarity	NPC322878
0.7006	Intermediate Similarity	NPC273755
0.6994	Remote Similarity	NPC161069
0.6988	Remote Similarity	NPC471820
0.6988	Remote Similarity	NPC240848
0.6988	Remote Similarity	NPC471821
0.6982	Remote Similarity	NPC39431
0.6978	Remote Similarity	NPC294951
0.6974	Remote Similarity	NPC190663
0.6968	Remote Similarity	NPC47667
0.6966	Remote Similarity	NPC476227
0.6966	Remote Similarity	NPC473402
0.6962	Remote Similarity	NPC130309
0.6961	Remote Similarity	NPC477637
0.6959	Remote Similarity	NPC220060
0.6957	Remote Similarity	NPC68865
0.6949	Remote Similarity	NPC328494
0.6949	Remote Similarity	NPC230611
0.6948	Remote Similarity	NPC46427
0.6948	Remote Similarity	NPC6975
0.6946	Remote Similarity	NPC129666
0.6944	Remote Similarity	NPC45037
0.6937	Remote Similarity	NPC141050
0.6933	Remote Similarity	NPC469426
0.6933	Remote Similarity	NPC469427
0.6928	Remote Similarity	NPC71684
0.6928	Remote Similarity	NPC145113
0.6923	Remote Similarity	NPC469444
0.6911	Remote Similarity	NPC473450
0.691	Remote Similarity	NPC137627
0.6909	Remote Similarity	NPC201244
0.6909	Remote Similarity	NPC477217
0.6889	Remote Similarity	NPC473001
0.6885	Remote Similarity	NPC471050
0.6885	Remote Similarity	NPC471048
0.6885	Remote Similarity	NPC471049
0.6883	Remote Similarity	NPC160493
0.6883	Remote Similarity	NPC252878
0.6878	Remote Similarity	NPC329295
0.6875	Remote Similarity	NPC209463
0.6872	Remote Similarity	NPC155506
0.6872	Remote Similarity	NPC26108
0.6872	Remote Similarity	NPC219350
0.6872	Remote Similarity	NPC159767
0.6872	Remote Similarity	NPC194699
0.6867	Remote Similarity	NPC81026
0.6865	Remote Similarity	NPC96275
0.686	Remote Similarity	NPC326349
0.686	Remote Similarity	NPC323336
0.6859	Remote Similarity	NPC101719
0.6859	Remote Similarity	NPC474479
0.6857	Remote Similarity	NPC189116
0.6845	Remote Similarity	NPC254798
0.6842	Remote Similarity	NPC314992
0.6842	Remote Similarity	NPC470546
0.6842	Remote Similarity	NPC244509
0.6842	Remote Similarity	NPC310467
0.6837	Remote Similarity	NPC478005
0.6836	Remote Similarity	NPC469904
0.6835	Remote Similarity	NPC111428
0.6826	Remote Similarity	NPC138775
0.6824	Remote Similarity	NPC262166
0.6818	Remote Similarity	NPC202521
0.6818	Remote Similarity	NPC469445
0.6807	Remote Similarity	NPC266741
0.6795	Remote Similarity	NPC222466
0.6791	Remote Similarity	NPC473305
0.6791	Remote Similarity	NPC163961

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC114806 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	111
0.1-0.2	318
0.2-0.3	721
0.3-0.4	1725
0.4-0.5	4130
0.5-0.6	1903
0.6-0.7	221
0.7-0.8	19
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8467	Intermediate Similarity	NPD8076	Discontinued
0.828	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6901	Phase 3
0.7925	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD8303	Discontinued
0.7654	Intermediate Similarity	NPD7523	Phase 3
0.7516	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD8019	Approved
0.7314	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3125	Approved
0.7294	Intermediate Similarity	NPD4565	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4564	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7495	Discontinued
0.717	Intermediate Similarity	NPD8173	Phase 2
0.717	Intermediate Similarity	NPD8172	Phase 2
0.716	Intermediate Similarity	NPD6681	Discovery
0.7134	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1330	Phase 2
0.7108	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD8416	Discontinued
0.6964	Remote Similarity	NPD7613	Discontinued
0.6959	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4177	Approved
0.6943	Remote Similarity	NPD4175	Approved
0.6895	Remote Similarity	NPD5856	Discontinued
0.6894	Remote Similarity	NPD8643	Discontinued
0.689	Remote Similarity	NPD7978	Discontinued
0.6872	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7342	Discontinued
0.6852	Remote Similarity	NPD5725	Approved
0.6852	Remote Similarity	NPD6073	Approved
0.6845	Remote Similarity	NPD6088	Approved
0.6845	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2217	Approved
0.6842	Remote Similarity	NPD2218	Phase 2
0.6839	Remote Similarity	NPD3072	Approved
0.6839	Remote Similarity	NPD3073	Approved
0.6839	Remote Similarity	NPD2584	Suspended
0.6839	Remote Similarity	NPD3071	Approved
0.6832	Remote Similarity	NPD4153	Approved
0.6821	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4214	Discontinued
0.6802	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7617	Discontinued
0.679	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4762	Approved
0.6774	Remote Similarity	NPD4761	Approved
0.6772	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1968	Approved
0.6766	Remote Similarity	NPD1967	Approved
0.6765	Remote Similarity	NPD4731	Phase 3
0.6755	Remote Similarity	NPD1348	Approved
0.6753	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD8162	Phase 2
0.673	Remote Similarity	NPD3040	Approved
0.6726	Remote Similarity	NPD8323	Discontinued
0.6711	Remote Similarity	NPD3123	Discovery
0.6709	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6852	Discontinued
0.6705	Remote Similarity	NPD8417	Discontinued
0.6688	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4152	Approved
0.6687	Remote Similarity	NPD5263	Approved
0.6687	Remote Similarity	NPD3908	Approved
0.6687	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4676	Approved
0.6687	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5747	Discontinued
0.6667	Remote Similarity	NPD7105	Phase 1
0.6667	Remote Similarity	NPD5042	Phase 1
0.6667	Remote Similarity	NPD6557	Phase 2
0.6646	Remote Similarity	NPD4794	Discontinued
0.6646	Remote Similarity	NPD3136	Phase 2
0.6627	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5296	Approved
0.6626	Remote Similarity	NPD5323	Approved
0.6612	Remote Similarity	NPD4092	Approved
0.6609	Remote Similarity	NPD2891	Approved
0.6608	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD4087	Phase 2
0.6588	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4125	Approved
0.6582	Remote Similarity	NPD4677	Discontinued
0.6576	Remote Similarity	NPD3999	Approved
0.6576	Remote Similarity	NPD3998	Approved
0.6576	Remote Similarity	NPD3997	Approved
0.6568	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4091	Approved
0.6556	Remote Similarity	NPD7484	Phase 3
0.6556	Remote Similarity	NPD7485	Phase 3
0.6552	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2014	Approved
0.655	Remote Similarity	NPD2013	Approved
0.655	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2016	Approved
0.6548	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6665	Discontinued
0.6541	Remote Similarity	NPD3518	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5367	Discontinued
0.6541	Remote Similarity	NPD6325	Discontinued
0.6534	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD8292	Phase 2
0.6522	Remote Similarity	NPD3991	Approved
0.6522	Remote Similarity	NPD3992	Approved
0.6522	Remote Similarity	NPD3993	Approved
0.6522	Remote Similarity	NPD3995	Approved
0.6522	Remote Similarity	NPD3996	Approved
0.6522	Remote Similarity	NPD3994	Approved
0.6506	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5299	Approved
0.6503	Remote Similarity	NPD3522	Approved
0.6494	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6058	Phase 2
0.6492	Remote Similarity	NPD5077	Approved
0.6492	Remote Similarity	NPD5076	Approved
0.6491	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD3519	Discontinued
0.6488	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6676	Phase 2
0.6471	Remote Similarity	NPD3016	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4151	Approved
0.646	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6967	Phase 2
0.6433	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4652	Approved
0.6424	Remote Similarity	NPD2583	Phase 2
0.6424	Remote Similarity	NPD6623	Phase 3
0.6421	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD1040	Phase 2
0.6417	Remote Similarity	NPD3990	Phase 3
0.6412	Remote Similarity	NPD5264	Approved
0.6412	Remote Similarity	NPD5265	Approved
0.641	Remote Similarity	NPD7282	Approved
0.6407	Remote Similarity	NPD6294	Approved
0.6407	Remote Similarity	NPD6295	Approved
0.6404	Remote Similarity	NPD7599	Phase 2
0.6391	Remote Similarity	NPD2088	Approved
0.6391	Remote Similarity	NPD2087	Approved
0.6389	Remote Similarity	NPD5219	Approved
0.6389	Remote Similarity	NPD5218	Approved
0.6384	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6689	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6646	Discontinued
0.6364	Remote Similarity	NPD7973	Discontinued
0.6364	Remote Similarity	NPD3989	Phase 3
0.6359	Remote Similarity	NPD8124	Phase 3
0.6359	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5614	Approved
0.6358	Remote Similarity	NPD5613	Approved
0.6358	Remote Similarity	NPD3987	Approved
0.6358	Remote Similarity	NPD3988	Approved
0.6347	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4738	Phase 2
0.6341	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD4173	Approved
0.6331	Remote Similarity	NPD4172	Approved
0.6328	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD8265	Approved
0.6323	Remote Similarity	NPD7508	Discontinued
0.6316	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD4557	Approved
0.6313	Remote Similarity	NPD4567	Approved
0.6313	Remote Similarity	NPD4566	Approved
0.6311	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7970	Approved
0.631	Remote Similarity	NPD4126	Approved
0.631	Remote Similarity	NPD5775	Approved
0.631	Remote Similarity	NPD5774	Approved
0.6307	Remote Similarity	NPD8315	Phase 1
0.6307	Remote Similarity	NPD4646	Approved
0.6307	Remote Similarity	NPD4647	Approved
0.6307	Remote Similarity	NPD4648	Approved
0.6306	Remote Similarity	NPD6093	Discontinued
0.6303	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5581	Approved
0.6301	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7720	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data